Remembering the greatest jazz album of all time, 50 years on

Jimmy Cobb is early. The sole surviving performer on Miles Davis's 1959 album Kind of Blue is waiting in a sixth-floor conference room just blocks from Columbia's old 30th Street Studios, the converted (Greek, Russian, or Armenian, depending on whom you ask) Orthodox church where the best-selling, most widely praised jazz album in history was recorded. The drummer and Harlem resident passes the time with his new iPhone—right now, unfortunately, it appears that if Cobb so much as stares at the gadget, it automatically calls his daughter. Thus far, hers is the only number programmed.

Sony Legacy is also early. In late September, the current keeper of the Columbia Records vaults unveiled its "super-deluxe" 50th-anniversary edition of Kind of Blue. But we're nearly as close to the album's 49th birthday, if we're going by release date. Yes, less than half a century ago (March 2, 1959, to be exact), Davis, Cobb, pianists Bill Evans and Wynton Kelly, saxophonists John Coltrane and Julian "Cannonball" Adderley, and bassist Paul Chambers—truly one of the most stellar lineups in jazz history—gathered for Blue's first sessions. "There wasn't a whole lot of preparation for me," says Cobb. "He [Davis] would just say, 'I want this one to sound like it's floating,' or something like that, you know. I didn't have any music for none of that stuff."

The group's second session, also on 30th Street, took place seven weeks later, and on August 17 of that year (Robert De Niro's 16th birthday), the album emerged. More than three million copies later, Kind of Blue stands not only as a landmark of accomplishment, but also of accessibility. Riding the coming crest of modal (you don't want to go there) musings over warm chordal arrangements, six (seven, technically) established yet efficient experts performed five superficially simple yet luxurious tunes. "It grabs all kinds of people," says Cobb. "To see how good those guys are, what they could do with just a little, that they could make it sound like that—you know, that's the thing. That's what it is. Just bring it down and it reaches everybody. There's something to that. It was just something that came along and clicked with everybody. It's just probably a once-in-a-lifetime thing."

Rob Trucks

Jimmy Cobb, standing alone

Despite its obvious legs, Kind of Blue exists in many ways as a mysterious, transitory moment in time. By its official release in August of 1959, Coltrane had recorded his own groundbreaking Giant Steps (another album with a Jimmy Cobb credit); Chambers and Adderley had quit the band over monetary disputes (a recurring theme with Davis); and Bill Evans, already on the outs, would soon be completely gone as well, upset (with good reason, it appears) over not receiving songwriting credit on "Blue in Green" and "Flamenco Sketches." Though Cobb remained in Davis's employ until just prior to 1963's Seven Steps to Heaven, the constant personnel changes may very well have contributed to Kind of Blue's seemingly atemporal state, transcending a mere two days spent within an Eastern European cathedral turned recording studio. "I don't know if he ever played all of those tunes off of that record live like that," Cobb says.

Yet despite having played on the most popular jazz album of all time, Cobb offers little further insight into the secret of Blue's success.

"Man, I don't think Miles even thought that it would have that longevity," he says. "If he even thought that that day, he would've asked for a pile of money. You know, if he thought that he had something that was going to really be selling for 50 years, he would've asked for real money."

As for the drummer, "I was probably the soberest one in the band," says Cobb, the only member of the Blue sextet other than Adderley to fully escape a heroin addiction. "And he knew I was going to be on time. And he knew when I got there, I would give 150 percent. So like that, you know. That's the pluses I had."

Asked what it felt like to join the group, he adds: "I was kind of leery. It's hard to get in a band behind [former Davis drummer] Philly Joe Jones, you know, because they're looking for Philly. It's almost like when we went to Philadelphia, and the people in Philly that were used to seeing [former Davis pianist] Red Garland looked up and saw Bill Evans, and they were wondering who he was. So I'm sure that when we went some places and Joe wasn't there and they saw me, they kind of felt the same way about it. So I was kind of nervous. I figured I was probably the weakest link there, because that's probably just the way I am, you know."

Raised in Washington, D.C., Cobb first hit the road at 21 with Earl Bostic and Dinah Washington, alongside future fellow Davis cohort Wynton Kelly. He soon found himself in New York City, living with Washington at 2040 Seventh Avenue. "It worked out pretty good," he recalls. "We did that for about five years. And during that time I meet everybody in show business, you know, because she was a big-time lady and I get introduced to everybody: Duke Ellington, Count Basie. Everybody you're supposed to know, I got to know them. In fact, 2040 was where Dizzy [Gillespie] lived."

Cobb's first involvement with Davis was helped along by his good friend Adderley. "At that time," Cobb says, "it was Joe and Red Garland and Coltrane, Cannonball and Miles. So a lot of times Joe wouldn't show up for gigs for one reason or the other. Or he just would be late. So Cannon was nervous, because he needed the money to pay off his bills, you know. So he used to tell me, 'Why don't you come around and sit with us, you know, and if Joe don't show, you can play, man. You'd be right there.' So I said, 'OK, I'm not really doing that much anyway.' So I go do that a few times. Then one time Joe didn't show up for a record date, you know, and I was there at the record date, and the record date was Porgy & Bess."

But Cobb's invitation to officially join the group came later. "I'm still not in the band," he continues. "But a little later, Miles talked to me. He says, 'You know, Joe's not in the band anymore. I want you to be in the band.' I said, 'OK.' So he told me all the particulars and stuff. Now it's six o'clock in the evening, and I'm in New York. So he's calling me and I don't know where he's calling me from. So I said, 'OK. Well, when you working? Where are you working?' And he said, 'Actually, we're working tonight.' I said, 'Oh, really? Where?' And he said, 'Boston.' So he's probably in Boston already. So I say, 'Boston?' He said, 'Yeah.' And it's 6:30, man. I say, 'Well, what time do you start?' He says, 'Nine o'clock.' I said, 'Nine o'clock? How am I going to get to Boston by nine o'clock, man?' He said, 'Man, you want the gig, don't you?' I say, 'Yeah, man.' I say, 'OK, I'll get there as fast as I can.'

"So I packed up the stuff, and at that time they had like a shuttle going from New York to Boston—55 minutes, you know. Takes me probably 55 minutes to get to the airport to fly 55 minutes, and a few more minutes to get from the airport in Boston to George Wein's club. That's where they were working, Storyville. So I get up there after scuffling like, you know, scuffling my heart out to get there, and they're playing on the stand, because it's probably 10 o'clock by now. So when I get there, they're playing the ballad 'Round About Midnight,' so I went up quietly and set up the drums. And, you know, there's an interlude in there."

Here, in a sixth-floor East Side conference room, Jimmy Cobb hums the "Round About Midnight" melody.

"I started right there. I played that with them. I was in the band—no rehearsals, no nothing. So that's the way it started, man."

The ending, however, has yet to be written. Jimmy Cobb, suitably enough, is at the forefront of the 50th-anniversary DVD. This month, the drummer will be recognized as a National Endowment for the Arts Jazzmaster. November brings appearances at Dizzy's Club Coca-Cola, as well as a number of dates in Germany. In January, Jimmy Cobb will turn 80 years old; in February, he'll be leading a new outfit, the So What Band, as part of Kind of Blue's continuing golden-anniversary celebration, still officially 11 months away.

But despite all the attention that comes with this territory—and having provided percussion on a work of acclaimed and enduring genius—it's the people he remembers, not the songs: "I'm proud to be here, man. I'm proud to be going on 80 years old. I never thought I'd be 80 years old. I'm here. I'm sorry that all my friends are gone, you know, but I've got them here."

And with that, the drummer pats his chest pocket. His hand lays over his heart, as well as his new iPhone, which presumably calls his daughter one more time.